3-(9H-Carbazol-9-yl)propan-1-ol
N Haridharan1, V Ramkumar, R Dhamodharan
1Department of Chemistry, IIT Madras, Chennai, TamilNadu, India.
Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
Summary
This study details the molecular structure of a novel organic compound, C(15)H(15)NO. Researchers identified specific dihedral and torsion angles, revealing a gauche conformation in the propanol side chain and intermolecular hydrogen bonding in its crystal structure.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical and physical properties.
- Intermolecular forces, such as hydrogen bonds, significantly influence crystal packing and material characteristics.
Purpose of the Study:
- To elucidate the precise molecular geometry and crystal structure of the compound C(15)H(15)NO.
- To investigate the conformation of the propanol side chain and the nature of intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
- Analysis of bond lengths, bond angles, and torsion angles provided detailed conformational information.
- Hydrogen bonding networks and crystal packing were characterized through crystallographic analysis.
Main Results:
- The dihedral angle between the two benzene rings was determined to be 2.25(2)°.
- The propanol side chain exhibited a gauche conformation, with a C-C-C-O torsion angle of -60.5(2)°.
- Molecules were linked into C(2) chains via O-H⋯O hydrogen bonds propagating along the [100] direction, with the hydroxyl hydrogen atom disordered over two equally occupied sites.
Conclusions:
- The study provides a detailed structural characterization of C(15)H(15)NO, highlighting specific conformational preferences and intermolecular interactions.
- The observed hydrogen bonding pattern and molecular arrangement offer insights into the solid-state behavior of this compound.
- The findings contribute to the broader understanding of structure-property relationships in organic crystalline materials.
More Related Videos
Related Concept Videos
03:02Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:16IUPAC Nomenclature of Carboxylic Acids
IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
02:36Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
01:16IUPAC Nomenclature of Aldehydes
Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...